A high yielding synthesis of optically active 3,5-disubstituted salicylidene β-amino alcohols (6) is described. The catalytic use of D or L- N-(3-phenyl-5-nitrosalicylidene)valinol in enantioselective sulfoxidation (H2O2 / VO(acac)2) gives up to 95% e.e. Asymmetric conjugate addition of thiophenol to 2-cyclohexen-1-one catalysed by Ti(OPr- i)4 and 6 leads to maximum 31% e.e. in the product.
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